Cetrorelix

Cetrorelix

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Subcutaneous injection
ATC code	H01CC02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	85%
Protein binding	86%
Elimination half-life	62.8 hours / 3mg single dose; 5 hours / 0.25 mg single dose; 20.6 hours / 0.25mg multiple doses
Excretion	feces (5% to 10% as unchanged drug and metabolites); urine (2% to 4% as unchanged drug)
Identifiers
IUPAC name Acetyl-D-3-(2´-naphtyl)-alanine- D-4-chlorophenylalanine-D-3-(3´-pyridyl)- alanine-L-serine-L-tyrosine-D-citruline-L- leucine-L-arginine-L-proline-D- alanine-amide
CAS Number	120287-85-6
PubChem CID	16130924
DrugBank	APRD00686
ChemSpider	10482082
UNII	OON1HFZ4BA
KEGG	D07665
ChEBI	CHEBI:59224
ChEMBL	ChEMBL1200490
CompTox Dashboard (EPA)	DTXSID7040996
ECHA InfoCard	100.212.148
Chemical and physical data
Molar mass	1431.06 g/mol
InChI InChI=1S/C70H92ClN17O14/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+/m1/s1 Key:SBNPWPIBESPSIF-MHWMIDJBSA-N

Cetrorelix acetate is an injectable gonadotropin-releasing hormone antagonist (GnRH antagonist). A synthetic decapeptide, it is used to treat hormone-sensitive cancers of the prostate and breast (in pre-/perimenopausal women) and some benign gynaecological disorders (endometriosis, uterine fibroids and endometrial thinning). In addition, cetrorelix is used in assisted reproduction to inhibit premature luteinizing hormone surges. The drug works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of LH and FSH. It is administered as either multiple 0.25 mg daily subcutaneous injections or as a single-dose 3 mg subcutaneous injection. The duration of the 3 mg single dose is four days; if hCG is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.

Use in IVF

Cetrorelix is marketed by Merck Serono as Cetrotide for use in in-vitro fertilization in all countries except Japan, where it is marketed by Shionogi and Nippon Kayaku. Aeterna Zentaris receives royalties on these sales and retains rights to develop cetrorelix for other indications. In IVF use it is injected daily after follicle stimulation has been initiated and evidence of follicle maturation is approaching; given daily it prevents an endogenous LH surge that would trigger an untimely ovulation prior to the hCG administration by the treating physician. As an alternative to the GNRH antagonist, also a GNRH agonist could be given, but agonist have to be started earlier to overcome the agonistic effect. Cetrorelix can be mixed with follitropin alpha without compromising their reported safety and efficacy.

Contraindications

The use of Cetrorelix is contraindicated in severe renal impairment. It is not intended for women aged 65 years or older. Use in women with severe allergic conditions is not recommended. Use with caution in women with active allergies or history of allergies.